Unexpected Formation of Allylic Hydroxylation Product in the Ozonolysis of N-[2-(Cyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide

Abstract

The ozonolysis of N-[(2-cyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide, followed by treatment with dimethyl sulfide gave a mixture of the expected keto aldehyde, 4-methyl-N-[2-methyl-6-(6-oxohexanoyl)phenyl]benzenesulfonamide and unexpected allylic hydroxylation product, N-[2-(6-hydroxycyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide.